2-O-[6-O-(3,3-dimethylbutanoyl)-β-D-galactopyranosyl]-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-O-[6-O-(3,3-dimethylbutanoyl)-β-D-galactopyranosyl]-glycerol
• 英文别名: [(2R,3R,4S,5R,6R)-6-(1,3-dihydroxypropan-2-yloxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,3-dimethylbutanoate
• 化学式: C₁₅H₂₈O₉
• 分子量: 352.382
• InChiKey: ODGCQXKBUKMBNA-FYGCWZCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-O-[6-O-(3,3-dimethylbutanoyl)-β-D-galactopyranosyl]-glycerol
  参考文献：
  名称：

  Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity

  摘要：

  Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-beta-D-galacto-sylglycerol (6'-position or 1,6' positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-beta-D-galactopyranosyll-sn-glyceroI (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.007

文献信息

• Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity
  作者：Diego Colombo、Laura Franchini、Lucio Toma、Fiamma Ronchetti、Reiko Tanaka、Junko Takayasu、Hoyoku Nishino、Harukuni Tokuda

  DOI：10.1016/j.ejmech.2006.07.007

  日期：2006.12

  Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-beta-D-galacto-sylglycerol (6'-position or 1,6' positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-beta-D-galactopyranosyll-sn-glyceroI (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion. (c) 2006 Elsevier Masson SAS. All rights reserved.